Field of the Invention
The present invention relates to novel polyaromatic propynyl compounds and to pharmaceutical/cosmetic compositions comprised thereof; the subject compounds are especially useful in human or veterinary medicine, or alternatively in cosmetic compositions.
The compounds according to the invention display marked activity in the fields of cell differentiation and proliferation, and are particularly useful in the topical and systemic treatment of dermatological conditions associated with a keratinization disorder, dermatological conditions (and the like) including an inflammatory and/or immunoallergic component, and dermal or epidermal proliferations, whether benign or malignant. The subject compounds can, in addition, be used for the treatment of degeneration diseases of the connective tissue, for combating skin aging, whether photoinduced or chronologic, and for treating cicatrization disorders. They are also useful for ophthalmological applications, especially for the treatment of corneopathies.
The compounds according to this invention can also be formulated into cosmetic compositions for body and hair care.
Briefly, the polyaromatic propynyl compounds according to this invention have the following structural formula (I): 
in which X is one of the radicals: 
wherein R10 and R11 are as defined below; Ar is a radical selected from among those of the following formulae (a)-(e): 
wherein R5 and R6 are as defined below; R1 is (i) a hydrogen atom, (ii) a radical xe2x80x94CH3, (iii) a radical xe2x80x94CH2xe2x80x94Oxe2x80x94R6, (iv) a radical xe2x80x94Oxe2x80x94R6, (v) a radical xe2x80x94COxe2x80x94R7, or (vi) a radical xe2x80x94S(O)tR9 wherein R6, R7, R9 and t are as defined below; R2 and R3, which may be identical or different, are each a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, a radical xe2x80x94OR6 or a radical xe2x80x94SR6, wherein R6 is as defined below, with the proviso that R2 and R3 may together form, with the carbon atoms from which they depend, a 5-or 6-membered ring optionally substituted by methyl groups and/or optionally interrupted by an oxygen or sulfur atom; R4 is a hydrogen atom, a halogen atom, a lower alkyl radical or a radical xe2x80x94OR6 wherein R6 is as defined below; R5 has the definition of R4, with the proviso that R4 and R5 may be identical or different; R6 is a hydrogen atom, a lower alkyl radical or a radical xe2x80x94COxe2x80x94R9 wherein R9 is as defined below and further wherein the radicals R6 may be identical or different; R7 is (a) a hydrogen atom, (b) a lower alkyl radical, (c) a radical of the formula: 
wherein Rxe2x80x2 and Rxe2x80x3 are as defined below, or (d) a radical xe2x80x94OR8 wherein R8 is a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, or a sugar residue, or an amino acid or peptide residue; R9 is a lower alkyl radical; R10 is a hydrogen atom, a lower alkyl radical, or a radical xe2x80x94OR6; R11 is a radical xe2x80x94OR6; Rxe2x80x2 and Rxe2x80x3, which may be identical or different, are each a hydrogen atom, a lower alkyl radical, a mono or polyhydroxyalkyl radical, an optionally substituted aryl radical or an amino acid or peptide or sugar residue, with the proviso that Rxe2x80x2 and Rxe2x80x3 may together form, with the nitrogen atom from which they depend, a heterocycle; t is an integer equal to 0, 1 or 2; and with the further proviso that the radicals R10 and R11 may together form a single oxo group of the formula xe2x95x90O.
This invention also features the salts of the compounds of formula (I) in the event that R1 is a carboxylic acid functional group, as well as the optical and geometric isomers thereof. When the compounds according to the invention are in the form of salts, they are preferably salts of an alkali or alkaline earth metal, or, alternatively, of zinc or of an organic amine.